Disclosed is a crystalline form of N-[[4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl]methyl]-4,6,7,9-tetrahydro-3-hydroxy-9,9-dimethyl-4-oxo-pyrimido[2,1-c][1,4]oxazine-2-carboxamide, sodium salt monohydrate. Also disclosed is at least one pharmaceutical composition comprising a crystalline form of N-[[4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl]methyl]-4,6,7,9-tetrahydro-3-hydroxy-9,9-dimethyl-4-oxo-pyrimido[2,1-c][1,4]oxazine-2-carboxamide, sodium salt monohydrate, and at least one method of using a crystalline form of to treat AIDS or HIV infection.
[[4-fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl]methyl]-4,6,7,9-tetrahydro-3-hydroxy-9,9-dimethyl-4-oxo-pyrimido[2,1-c][1,4]oxazine-2-carboxamide, sodium salt monohydrate, which has the structure of Formula (I):
referred to herein as “Compound (I)”, may be effective in treating AIDS or HIV infection. In at least one instance, Compound (I) was found to potently bind to and act as an antagonist to HIV integrase. Compound (I) is disclosed in U.S. Pat. No. 7,176,196, wherein said disclosure is hereby incorporated herein by reference.
Typically, in preparing a pharmaceutical composition, a form of the active ingredient is sought that has stability in handling. A difficulty regarding the free acid of Compound (I) is that it has a high susceptibility to ignition and risk for explosion. The present invention provides a form of Compound (I) that surprisingly affords a safer set of properties that can be useful in the manufacture of Compound (I).